Phosgene → Benzene, 1-isocyanato-2-methoxy-

HRID 483275Notes

Reaction equation

[C:1](Cl)(Cl)=[O:2].[CH3:5][O:6][C:7]1[C:8]([NH2:13])=[CH:9][CH:10]=[CH:11][CH:12]=1>ClC1C=CC=CC=1>[CH3:5][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N:13]=[C:1]=[O:2]

Participants

Conditions

Temperature: 125 °C

Procedure

Into a 2 liter three-necked flask equipped with a dry ice condenser and an overhead stirrer, was condensed 100 ml of phosgene. At - 5° C., was added a solution of 25 g (0.2032 moles) of o-anisidine in 350 ml of chlorobenzene and a heavy white precipitate was observed. The mixture was then heated at 125° C. for three and a half hours while passing phosgene slowly through the solution for the first hour and a half, and then nitrogen for the last two hours. The solution was then distilled to afford 27.0 g (89%) of o-methoxyphenyl isocyanate, bp 74°-76° C. at 3 mm Hg. 'H NMR (δ,CDCL3) 6.7-7.1 (multiplet, 4H) and 3.80 (s, 3H).

Workup

customInto a 2 liter three-necked flask equipped with a dry ice condenser and an overhead stirrer
customfor the last two hours
distillationThe solution was then distilled

Sources & evidence

ORD record: ord-70201d39ee374ad6a4a22aafeaf17ddf
Source dataset: uspto-grants-1986_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04578514

Reaction notes

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